Perfume-emitting materials



Patented Mar. 31, 1936 UNITED STATES PATENT OFFICE PERFUME-EMITTING MATERIALS Walter Christian Meuly, New Brunswick, N. .L.

assignor to El. du Pont de Nemours & Compony. Wilmington, Del., a corporation of Delaware No Drawing. Application December 8, 1933, Serial No. 701,569

8 Claim.

This invention relates to a novel method of increasing the cost thereof. For instance when,

perfume was added to ordinary'soap it was necessary to add about one percent by weight in order that it would not be completely dissipated before the soap was used. In the case of fine soaps about two to three percent of perfume was added. Obviously this increased appreciably the cost of production, and made its use in low priced cleansers prohibitive. As is well known such cleansers possess a disagreeable odor, and would be much more acceptable if it were possible to mask suchodor with a pleasant-smelling perfume.

It is an object of this invention to permit the use of perfumes in cleansing media and other alkaline material in much smaller quantities than was heretfore possible. A further object is to prevent suchperfumes from being dissipated prior to use. nomically possible to use such compolmds in'low priced cleansers in order that the disagreeable odor thereof will be completely masked. Additional objects will become apparentfrom a consideration of the following description.

'll'hese objects are attained according to the herein described invention which in its preferred embodiment comprises incorporating a small amount of the bisulflte derivative of an aldehyde or ketone perfume in a substantially dry alkaline medium which is capable of liberating the original perfume upon addition of water.

we invention may be more readily understood by a consideration of the following illustrative examples, in which the quantities are stated in parts by weight.

Example 1 To i000 parts of soap powder were added 2 parts of finely powdered benzaldehyde bisulflte compound. The substances were thoroughly mixed. The soap powder remained substantially unperfumed. A small amount (about 1 gram) of the mixture was added to a little water in a beaker, on touching the water the pleasant odor of bitter almonds became at once-noticeable and masked effectively the unpleasant odor of the soap powder A still further object is to make it ecosolution which was quite pronounced in a similar experiment where the benzaldehyde bisulflte compound had been left out. The use of cold or hot water gave the same improved result.

The mixture of soap powder and benzaldehyde bisulfite was kept for 6 months to test the stability of the combination. When brought into contact with water, the almond odor was noted in undiminished strength. I

Example 2 A mixture of 1000 parts of soap powder and 3 parts benzaldehyde bisulflte was tested in household work (cleaning of dishes). The unpleasant odor of the soap powder was found to be successfully covered by a pleasant odor of bitter almond.

Example 3 Example 4 Citral was transformed into normal citral bisulilte by treating with sodium sulilte and sodium bicarbonate. 3 parts of n this compound imparted a very pleasant lemon odor to 1000 parts of soap powder as soon as the mixture was brought into contact with water.

Example 5 The b isulflte compound of heptylic aldehyde was added to soap powder in the proportion of 5 parts per 1000. In the presence of water the characteristic note of oenanthol appeared at once.

Example 6 The ketone, alpha ionone, was transformed into its crystallized blsulflte derivative and incorporated into soap powder. A concentration of 3 parts to 1000 parts was suflicient to give a scent of violet to the powder upon addition of water.

Example 7 By replacing the soap powder in Example 1 with anhydroussoda ash a mixture was obtained which.v in water developed the perfume of bitter almonds.-

In place of or in addition to the foregoing... alkaline materials other compoundssuch ashore):- and triscdium phosphatemay housed wlthsatia factory resutts.

. class of these compounds, and are not intended as a limitation upon the scope of this invention. In place of these compounds numerous other aldehyde and ketone perfumes may be used with excellent results. These compounds may be members of the aromatic, aliphatic, isocyclic or heterocyclic series, the only requirement being that they possess odor and are capable of forming bisulfite derivatives from which the original odor-emitting compound may be regenerated by the action of an aqueous alkali. A few of the compounds falling within this category are citral, citronella, hydroxycitronella, benzaldehyde, cinnamic aldehyde, heptylic aldehyde, pulegon, ionone and methyl-ionone.

Bisulfite derivatives of the various aldehyde and ketone perfumes may readily be prepared by reacting the perfume with the bisulfite compound,

. preferably an alkali-metal bisulfite. These com pounds are incorporated inthe alkaline medium in the dry state. The alkaline medium should also be substantially dry in order that the perfume derivatives will remain unchanged until used. It is advisable that the compositions described herein be prepared and maintained in an anhydrous condition until ready for use.

The material to be perfumed should have sufficient alkalinity to decompose the bisulfite compounds and regenerate the original perfume upon the addition of water. Soap powders and flakes when substantially water-free are excellent illustrations of such media, and may be used with very satisfactory results. However, the invention is not limited thereto since many other compounds possess the property of regenerating the original perfume upon the addition of water. Among these compounds mention may be made of soda ash, .borax, sodium resinate, and trisodium phosphate, it being understood that these materials are representative only of the largegroup of substances possessing this characteristic.

Bisulflte derivatives of perfumes have never before been incorporated with alkaline materials in order to impart odor thereto since such derivatives are well known to be odorless. By means of the instant invention this odorless property is utilized in a novel manner to produce the exceedingly advantageous result of conserving the perfume until it is actually used. Despite the fact that the amount of the bisulfite derivatives utilized is so exceedingly small the perfumeemitting properties of thematerials are highly satisfactory since such properties are conserved practically undiminished .until actual use. Furthermore, although aldehydes and ketones were possessed of very strong and pleasant odors their use in alkaline media such as soaps was formerly not recommended because of their susceptibility to oxidation, polymerization or disintegration in.

the presence of such media. In the form of the bisulfite compounds however they may be kept in contact with alkaline materials practically indefinitely, without destroying to any noticeable extent their valuable odor-emitting properties.

It is to be understood that the amount of perfume derivative added according to the present invention is capable of considerable variation and modification. In general 2-5 parts of such derivative per 1000 parts of material to be perfumed give satisfactory results. However, such figures are not to be construed as a restriction since they may be varied within much wider limits without departing from the scope of the present invention. The amount added will depend to a great extent upon the material in which it is to be incorporated and theparticular perfume derivative utilized, and may vary from a trace to as high as several percent. It is, of course, apparent that the bisulfite derivatives of more than one aldehyde and/or ketone perfume may be incorporated into any given material. Two or more of such derivatives may be incorporated in order that the resulting odor-emitting properties will be a blend of the individual odors of the several components.

As many apparently widely difierent embodiments of this invention maybe made without departing from the spirit and scope thereof, it is to be understood that the invention is not limited to the specific embodiments thereof except as defined in the appended claims.

I claim:

1. A process for producing perfume-emitting materials which comprises forming the bisulfite compound of a member selected from the group consisting of aldehyde and ketone perfumes and adding said bisulfite compound to an alkaline detergent capable of liberating the original perfume upon addition of water, the aforementioned compounds being in a substantially anhydrous condition.

2, Aprocess for producing perfume-emitting materials which comprises forming the bisulfite compound 'of a member selected from the group consisting of aldehyde and ketone perfumes and adding said bisulfite compound to a member selected from the group consisting of soap powder, soda ash, borax, and trisodium-phosphate, the aforementioned compounds being in a substantially anhydrous condition.

3. The process of claim 2 wherein the perfume derivative is selected from the group consisting of bisulfite-compounds of citral, citronellal, hydroxycitronella, benzaldehyde, cinnamic aldehyde, heptylic aldehyde, pulegon, ionone, and methylionone.

4. Perfume-emitting materials which comprise the bisulfite compound of a member selected from the group consisting of aldehyde and ketone perfumes in admixture with an alkaline detergent capable of liberating the original perfume upon addition of water.

5. Substantially dry perfume-emitting materials which comprise the bisulfite compound of a member selected from the group consisting of aldehyde and ketone perfumes in admixture with a mem- 8. Materials capable of emitting perfume uponwetting which comprise the reaction product of benzaldehyde and sodium bisulfite in admixture with analkaline soap.

, WALTER C. MIEULY. 

